Shelter Island Vacations from ₩603,186

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was ₩860,682, price is now ₩603,186 per person
₩603,186
per person
Feb 4 - Feb 6
found 8 hours ago
Roundtrip flight included
Las Vegas (LAS) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
The hotel has a modern feeling, which was great. The room had plenty of space for a couple. The staff was very courteous and friendly. The downstairs "grab and go café" we loved. The coffee options were great and very reasonable priced. There are 2 negatives for our stay. The room door slams closed if you don't hold it, which will wake you, if your neighbors come home late. Also we stayed at the 25th floor, which in the morning it took twice almost 10 min for the elevator to arrive. But with that being said, it would not stop us though from coming back to this property!

Reviewed on Dec 17, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ₩911,701, price is now ₩628,188 per person
₩628,188
per person
Feb 4 - Feb 6
found 8 hours ago
Roundtrip flight included
Las Vegas (LAS) to New York (JFK)
9/10 Wonderful! (2,790 reviews)
Nice rooms. Clean, staff friendly.

Reviewed on Dec 17, 2025

The William Vale

The William Vale

5 out of 5
Price was ₩1,031,048, price is now ₩755,326 per person
₩755,326
per person
Feb 4 - Feb 6
found 8 hours ago
Roundtrip flight included
Las Vegas (LAS) to New York (JFK)
8.8/10 Excellent! (1,002 reviews)
The room was nice and so comfortable. The area of the hotel is awesome with plenty to do. I had dinner at the west light the food was amazing. I would love to come back in the summer to check out the pool. I would work on the front desk staff being a bit more friendly and attentive.

Reviewed on Dec 4, 2025

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Price was ₩920,895, price is now ₩686,726 per person
₩686,726
per person
Feb 4 - Feb 6
found 8 hours ago
Roundtrip flight included
Las Vegas (LAS) to New York (JFK)
9/10 Wonderful! (3,569 reviews)
Clean room , great views , friendly service

Reviewed on Dec 17, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was ₩861,580, price is now ₩643,906 per person
₩643,906
per person
Feb 4 - Feb 6
found 8 hours ago
Roundtrip flight included
Las Vegas (LAS) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
Hotel has little extras that are appreciated. Wonderful stay.

Reviewed on Dec 17, 2025

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩575,972 per night from Jan 12 to Jan 13
₩575,972
₩789,658 total
Jan 12 - Jan 13, 2026
includes taxes & fees
8.2/10 Very Good! (701 reviews)
Everything was perfect. Staff, room, experience. Will definitely stay again.

Reviewed on Dec 14, 2025

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ₩268,479 per night from Dec 21 to Dec 22
₩268,479
₩334,184 total
Dec 21 - Dec 22
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Holiday family tradition!

Reviewed on Dec 12, 2025

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,003 reviews)
Nice, pet friendly facility with an amazing Indian restaurant next door!

Reviewed on Dec 14, 2025

Get rates
Pier Blue Inn Old Saybrook - Essex
See all 4,676 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.